


Mutual Understanding

by DRHPaints



Series: Kinky Bill One Shots [8]
Category: American (US) Actor RPF, Bill Hader - Fandom, Bill Hader RPF, US Comedians RPF
Genre: Anal Fingering, Anal Sex, Cum Play, Established Relationship, Explicit Language, Explicit Sexual Content, F/M, One Shot, Other, Smut, Trans, Trans Character, Trans Female Character
Language: English
Status: Completed
Published: 2020-08-19
Updated: 2020-08-19
Packaged: 2021-03-06 03:01:24
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,149
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25996414
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Bill brings his lover Michelle, who is trans femme, to the It: Chapter 2 premiere and after they go home, make love, and engage in some light cum play.
Relationships: Bill Hader/Original Trans Character, Bill Hader/Original TransFemale Character, Bill Hader/Original TransFemme Character, Bill Hader/Original TransWoman Character
Series: Kinky Bill One Shots [8]
Series URL: https://archiveofourown.org/series/1877902
Kudos: 3





	Mutual Understanding

**Author's Note:**

> TW/CW: The original character of Michelle is assigned male at birth and has not had bottom surgery. I did my best to steer clear of dysphoria-inducing language (I am a trans author) but I do make reference to her ‘length’ ‘tip’ and ‘head.’ Please use your own judgement as to whether or not this story is right for you. Thank you.

Inserting the second earring, Michelle appraised herself in the mirror. As much as she enjoyed the excuse to get all gussied up, events like this made her nervous. Michelle knew she passed, it had been years since a stranger misgendered her, but being photographed in public with Bill still made her uneasy. Like Bill she, too, stayed off of social media, so she never saw any comments from the trolls, and the one time a tabloid rag had used a hateful word about her at the beginning of their relationship, Bill exploded, springing into action and hiring a team of lawyers, letting all future publications know he was not to be fucked with as far as this matter was concerned.

But as Michelle adjusted herself in her flowing purple gown, double checking her eyeliner, it frustrated her that it was even an issue. It never had been for Bill, thank goodness. When they met while she was doing press for her book, and Bill started to chat her up, making her laugh so hard she had tears in her eyes, he asked her out for coffee, and she explained right away. Michelle was always up front about being trans, as long as it was safe to do so. She found it lessened later complications.

Bill just shrugged. “Okay then.” And went back to his story about being inadvertently fed peanut butter when he had no epipen at his disposal. That’s how it always was with Bill. In public, in the bedroom; a non-issue. And Michelle loved him for it.

Unfortunately the people around them didn’t necessarily feel the same way. When they started dating, Bill introduced Michelle around to his family and friends, and they discovered her books, realizing she was trans. A handful of them fell away. Initially Michelle apologized, telling Bill she was sorry that she caused him to lose people and disrupt his life. But Bill took her face in both hands, cobalt blue eyes staring at her intently.

“If they can’t handle us being together, they weren’t my friends in the first place.”

Smoothing over her dress, Bill’s smiling face appeared in the mirror, resting on her shoulder and wrapping his arms around her waist from behind. 

“Hey babe,” he pressed a kiss just below her ear. “Are you almost ready? You’re so beautiful.” He looked at their reflection in the mirror and gently swayed them back and forth.

Nodding, Michelle turned back to give him a quick peck. “Yup, just one minute.” Giving herself a last glance and fluffing her scarlet hair, Michelle turned off the bathroom light and her heels clicked into the living room.

“Damn, you’re looking sharp.” She slid a finger under one of Bill’s suspenders before he pulled on his navy suit jacket.

“Aw, thanks hun.” He gave her a wide grin with those light pink lips that made her crazy. “Car’s here. You good?”

“Yup.” Michelle smiled. Bill patted her ass lovingly and they made their way out the door. 

Noticing Bill’s hands crawling in his lap in the backseat, Michelle squeezed one of his thick thighs. “It’s gonna be great, Bill. Believe me.”

“Yeah. Yeah, okay…” Bil nodded, but his eyes were darting around the interior of the car and outside the window, not looking at her.

“ _ Bill, _ ” she murmured softly, taking his chin in hand until his stormy blue eyes met her own. “Look at me. It’ll be wonderful. Let’s take a breath.” As they often did when one, or both, of them was anxious, they inhaled in tandem, releasing it slowly. Repeating it a couple of times, Michelle saw Bill’s shoulders drop.

“Thanks.” He closed his eyes and nodded. “I needed that.”

Arriving at the theatre, Bill stepped out of the car to the cacophony of celebrities, cameras, and reporters; holding out a hand to assist Michelle. Walking down the red carpet with an almost painful smile plastered on her face, there wasn’t a moment when Bill wasn’t touching her. Hand on the small of her back, arm around her, entwining their fingers. 

Every so often he would lean into her ear and ask. “Are you okay?” Or “Do you need anything?” To make sure she wasn’t overwhelmed by the circus. Even though Michelle knew Bill found it almost as difficult to deal with as she did.

Finally getting inside and locating their seats, Bill held Michelle’s hand and smiled at her nervously as the house lights went down. Watching intently, Michelle swelled with pride at the performance of her brilliant, beautiful man. Some parts of the film were too much for her and she had to close her eyes, which couldn’t help but remind her of when Bill impersonated Shephard Smith during his time on Saturday Night Live.  _ Well, mark me down as scared AND horny! _

When the credits rolled Michelle had tears streaming down her face and as the lights rose, Bill looked to her with concern.

“Honey, what’s wrong?”

Michelle shook her head. “Nothing’s  _ wrong _ , Bill. You were just amazing. It got to me, is all.” She rummaged in her tiny purse for a tissue and wiped her face.

“Aw, you’re sweet.” Bill kissed her temple. Composing herself a bit, Michelle stood by patiently while Bill did some interviews, and then finally they arrived home. 

Unhooking the surprisingly heavy earrings and tossing them on the dresser, Michelle rolled her neck before unclipping her hair and shaking it loose. Bill came up behind her, wide palms kneading her ass as he pressed a kiss to her shoulder.

“Mmm...babe, let’s get you out of that dress.” He hummed.

Michelle grinned, hand trailing up to scratch the dark stubble under his sharp jaw. “Be my guest.” Pulling her crimson hair aside, Bill pulled down the zipper and she stepped out of her gown, tossing it over a nearby chair. Turning to him, she pushed the jacket off of Bill’s broad shoulders, catching his mouth in a kiss as she removed his suspenders and loosened his tie. 

One large hand cupped her face and the other massaged her breast over the black lace bra as Bill tilted his head to deepen their kiss, tongue dancing in her mouth and humming appreciatively against her lips. Exposing his firm chest, Michelle’s fingertips trailed over his sparse dark chest hair while he discarded her bra, walking her backward to the bed. Before her knees hit Bill scooped her into his arms and laid her down, undoing his slacks and allowing them to puddle to the floor along with his boxers, exposing his massive erection before climbing on top of her.

Lowering himself, Michelle let out a soft sigh of pleasure as Bill’s weight settled on top of her, spreading her legs to accommodate him, his cock brushing between her legs. Bill’s mouth moved against hers passionately, sizable hands roaming over her skin like currents of electricity, charging her and alighting every inch of flesh.

“You’re so fucking beautiful.” Bill’s breath was warm against her ear as he kissed and nipped at the sensitive skin of her neck, starting to grind himself between her legs. Caressing her breasts, Bill tweaked a nipple between his thumb and forefinger before dipping down to suck it between his lips. 

Returning to her mouth, their tongues wove together before Bill broke away, combing her auburn hair back from her face. “You want me to fuck you, babe?”

Michelle was already breathing hard. “Yes, Bill. Fuck me. Please.”

Nodding, Bill peppered kisses along her jawline and down to the hollow of her throat before reaching over to rifle through their bedside drawer, retrieving the lube. Scooting down on the bed, he grabbed the waistband of Michelle’s panties and peeled them off, letting them flutter to the floor, revealing her. Applying some to the fingers of each hand, Bill first began to use his thumb to circle the head of her length in the way he knew she liked; with aching slowness, precision, and patience. 

Michelle bit her lip as Bill’s other hand began rubbing two fingers over her entrance, teasing the tight muscle for a few minutes before sliding inside. He curled his lengthy fingers upward and flicked until her mouth dropped open and her muscles jumped. Bill smirked as he watched her reaction, feeling as if he were playing a video game, hands on a remote and watching Michelle on the screen, able to control her every move with the simple push of a button.

Pulsing his fingers inside of her, Bill observed as Michelle’s hands bunched in the sheets, moans rising, diggging her heels into the mattress and rocking her hips down in an effort to fuck herself on his fingers. 

“ _ Oh Bill, oh yes! Just like that! _ ” She panted, head thrown to the side as his thumb sped up on her tip.

“Am I making you feel good, beautiful?” Bill asked in a low, sultry voice. “Do you want me to make you cum like this, or do you want me to fuck you?” 

Straining, Michelle knew she only had a couple of moments before the decision would be made for her. “ _ I want you to fuck me, Bill. Fuck me! _ ”

Quickly withdrawing, Bill lubed his cock and pushed the head between her legs. “You ready for me, babe?” Michelle nodded enthusiastically and Bill surged forward slowly until his hips were flush against her, Michelle gasping and back arching as his thick cock filled her.

“Fuck, babe, I love being inside of you.” Bill groaned, eyes closed and head thrown back, strong hands kneading her creamy thighs. Bill swiveled his hips, angling upward so he would strike Michelle’s special spot with every stroke, and returned his thumb to her sensitive tip, rotating in time with their movements.

Placing his free hand beneath her ass, Bill lifted her so he could pound into Michelle recklessly, and she braced herself with her heels, pistoning herself against his stiff cock as her moans rose to screams.

” _ Yes, Bill! Fuck me! FUCK ME! _ ” Michelle could feel the threat of her orgasm approaching and her thighs shook. Had Bill’s hand not been elevating her, she would’ve collapsed as her body constricted around him, eyes rolling while Bill’s name repeatedly tumbled from her painted lips.

A broken moan escaped Bill at the sudden pressure around his cock and he dropped Michelle, falling forward on top of her as his hips continued to ram forward.

“ _ Michelle, babe, I’m gonna cum, I’m gonna fucking cum _ .” He gasped, voice high and irregular, forehead pressed against hers.

” _ Yeah, Bill, cum inside me. I want your cum. I love it. Fill me with your cum, Bill. _ ” She whispered.

With a strangled cry, Bill shot forth, cradling her head in both hands, an expression near anguish on his face before he relaxed above her. Fighting for oxygen, Bill kissed her cheek.

“That was great. I love you, beautiful.”

“I love you, too, Bill.” Michelle locked her legs around him, holding him close as they both came down. 

Eventually Bill extricated himself, and as he pulled out his cock he stared at the thick, white cum dripping out of Michelle.

“ _ Fuck _ that’s hot.” Bill licked his lips, wiping his sweaty forehead.

Michelle looked at him, blinking. “What is?”

“You filled with my cum. I don’t know, babe, it’s just...it’s getting me all excited for some reason.” He rubbed a smirk away from his stubbled mouth.

Michelle gave a half chuckle. “Oh yeah?”

“Yeah…” Bill started drawing small patterns on her spread thigh. “Would you mind if I...clean you up with my mouth?”

Raising an eyebrow, the corner of Michelle’s mouth twitched. “No, not at all.”

“And what if, um…” Bill’s fingers tiptoed between her legs. “What if once I have it in my mouth...could I kiss you? Do you want to taste it, too?”

Michelle bit her lip. “Sure, Bill. Let’s try it.” Bill tipped his head down and looked at her up through his eyelashes in that almost coquettish way that made her arousal for him insatiable before dipping his head down and guiding her legs further apart.

Sturdy jaw digging forward, Bill lapped away and Michelle lost herself in the sweet sensation, his talented tongue pushing as deep inside her as he could manage while he slurped his seed from inside and licked up the dripping trail.

Rising with a silent mouthful, Bill crawled up to her, fingers gliding over her body before he fused their lips together. Mouth opening under his, Michelle’s tongue was flooded with the sweet, salty taste of him, so familiar and yet slightly different when mixed with herself and Bill’s saliva. A small rivulet trickled down her chin as they kissed, each swallowing half and holding one another near. 

Parting, Bill kissed her nose sweetly. “Thanks for everything today. I couldn’t get through it without you, beautiful.”

Michelle played with his short chestnut locks. “Anytime.” 

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom


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